I just sold my 1997 Dakota recently after owning it for about 7 years. Mine was a 2WD extended cab Sport with the 3.9L V6 and an automatic. Here's my take:
The Good:
-The size is great. It's bigger than a contemporary S10/Ranger, but smaller than full size. I found it to be perfect.
-The interiors hold up better than their contemporaries. Although mine had plenty of creaks and rattles, the seats and dash were flawless after nearly 180k miles.
-Drivetrain options are pretty good. They range from the Jeep 2.5L I4 to the 5.9L V8 in the R/T trucks. I'd also avoid the 4.7L as others have said. There are also tuning options for the 5.2L and 5.9L out there. The 3.9L V6 in mine was adequate, but I always wished it had a V8. I'd get a 5.2 truck if you are looking for 4WD, or hold out for a 5.9 R/T if 2WD is what you want.
-I think they still look great, but that's entirely subjective.
-They have rack and pinion steering, which feels pretty good on these.
The Bad:
-90's Chrysler build quality was extremely hit or miss. I had issues with random wiring, parts fitment, etc. Mine was one of the early trucks, though.
-They eat ball joints and other front end components, like many of the contemporary small trucks and SUV's.
-Steering shafts on these have a proprietary u-joint and when they start to fail (and they do so often), you have to replace the entire thing. It's a pain to do, especially on 4WD trucks. Mine was so bad that it was a miracle I didn't crash!
-Rust, rust, rust. These trucks love to rust, especially the fenders, rockers, and bedsides. Bumpers also love to rot out. Mine were skeletal remains when I bought the truck!
-Speaking of rust, look out for rusty brake lines. Mine only retained the original lines on the ABS pump; everything else I had to replace, and sometimes twice! They were also built in that funky period where US OEM's were using some standard and some metric, so you'll get brake lines with bubble flares with SAE and/or Metric fittings, which is extra fun. Also, they don't make pre-bent lines, so get used to fabbing them up yourself. I got pretty good at it over the years because of my truck.
-They have an odd 6-lug bolt pattern, so finding aftermarket wheels can be tough. They did make OEM wheels in everything from steel 15's to 17's from the R/T trucks, which is nice.
-Lighting is AWFUL. The headlights aren't clear, and light output on mine was about as good as duct taping a free Harbor Freight flash light with a failing battery to the hood, even with upgraded bulbs. I could drive around with my high beams on and no one would notice. They do make aftermarket housings for them, but I'm not sure how much better they would be.
-Even the small engine models are terrible on gas. The best I got out of the V6 was about 16mpg once. Typically, I'd get between 14 and 15mpg. You might as well skip the smaller engines and get a V8 truck, because they will get the same gas mileage.
All that said, they are a good bargain if you can find a clean one. I'd stick to one with the 5.2 or 5.9 V8, make sure you are good at fabbing up brake lines, and find the cleanest one you can!